Hydrochloric Acid → HCID 59253266, compound

HRID 643695Notes

Reaction equation

HRID 643695 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]([CH3:23])([CH3:22])[C:18]([O:20]C)=[O:19])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO.O1CCCC1>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]([CH3:22])([CH3:23])[C:18]([OH:20])=[O:19])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59253268HCID 59253268, compound

Product 1

HCID 59253266HCID 59253266, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropanoate (Step G, 1.07 g, 2.64 mmol) in methanol (5 mL) and tetrahydrofuran (5 mL) was added 2N sodium hydroxide aqueous solution (5 mL) at room temperature. The mixture was stirred at room temperature for 3 h. The mixture was made acidic with 2N hydrochloric acid (pH ˜4) and concentrated under reduced pressure. The residue was dissolved in water (50 mL) and dichloromethane (50 mL). The aqueous layer was separated and extracted with dichloromethane (50 mL×2). The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound (920 mg, 89%) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water (50 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with dichloromethane (50 mL×2)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-865b343fb78842be8fdd81404c4c7127
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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